Ammonium Hydroxide → HCID 69601970, compound

HRID 1940075Notes

Reaction equation

HRID 1940075 reaction equation
[C:1]1(=[O:22])[N:5]([CH:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][C:8](O)=[O:9])[C:4](=[O:17])[C@H:3]2[CH2:18][CH2:19][CH2:20][CH2:21][C@@H:2]12.C(N1C=CN=C1)([N:25]1C=CN=C1)=O.[OH-].[NH4+]>O1CCCC1>[C:1]1(=[O:22])[N:5]([CH:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][C:8]([NH2:25])=[O:9])[C:4](=[O:17])[C@H:3]2[CH2:18][CH2:19][CH2:20][CH2:21][C@@H:2]12

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 15435489HCID 15435489, compound

Product 1

HCID 69601970HCID 69601970, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(cis-hexahydrophthalimido)-3-phenylpropionic acid (0.903 g, 3.00 mmol) and carbonyldiimidazole (0.525 g, 3.75 mmol) in 13 mL of anhydrous tetrahydrofuran under nitrogen was stirred for 1 hour, then 0.25 mL of concentrated ammonium hydroxide was added to the reaction solution. After 20 minutes, the reaction mixture was concentrated in vacuo to an oil. The oil was diluted with 20 mL of water and the mixture extracted with ethyl acetate (20 mL). The organic layer was dried (sodium sulfate) and concentrated to afford an oil. The oil was then purified by flash chromatography (silica gel, 5/95 methanol/methylene chloride, Rf =0.3) to afford 210 mg of 3-(cis-hexahydrophthalimido)-3-phenylpropionamide as an oil which slowly crystallized to an ivory solid: 1H NMR (DMSO-d6) d7.49 (s, 1H, NH), 7.4-7.2 (m, 5H, Ar), 6.90 (s, 1H, NH), 5.54 (t, 1H, J=7.8 Hz, CH), 3.09 (d, 2H, J=7.8 Hz, CH2), 2.95-2.80 (m, 2H, CH2), 1.8-1.1 (m, 8H); 13C NMR (DMSO-d6) δ179.6, 179.5, 171.5, 139.5, 128.6, 127.7, 127.2, 55.2, 50.6, 38.8, 36.5, 23.4, 23.3, 21.5.

Workup

  1. waitAfter 20 minutes
  2. concentrationthe reaction mixture was concentrated in vacuo to an oil
  3. additionThe oil was diluted with 20 mL of water
  4. extractionthe mixture extracted with ethyl acetate (20 mL)
  5. dry with materialThe organic layer was dried (sodium sulfate)
  6. concentrationconcentrated
  7. customto afford an oil
  8. customThe oil was then purified by flash chromatography (silica gel, 5/95 methanol/methylene chloride, Rf =0.3)

Sources & evidence

ORD record
ord-ead6ca0f007e4e28a968a17d3e48d538
Source dataset
uspto-grants-1997_12
Patent number
US05698579

Reaction notes

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